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Appearance and Personality
Miss Josephine Barry is an educated woman who has lived life to the full, surrounded by artists of all sorts. Raised in a rigid conservative family, Josephine was indoctrinated to repress her passions and dreams until she met Gertrude. Falling deeply in love with each other, Josephine blossomed becoming more open to the beauties of life. Josephine is, however, rather skeptical and difficult to cheat and can be quite firm in her belief. Josephine is also an avid reader and doesn't like when someone spoil her the plot of novels she's reading. Josephine is a great comforter, and her kindness struck Anne to the point where she considered Josephine to be a kindred spirit.
Miss Josephine Barry did not approve of Anne and her ways when they first met. She changes her mind when Anne saves Minnie May’s life.
Josephine has a fierce exterior but finds a soft spot for Anne, her grand niece Diana and her friends. She encourages their great adventures either financially, in kind or emotionally.
When the Cuthberts were in dire financial straits and had to terminate the services of Jerry, their farmhand, Josephine decides to hire him and informs him that his place of work will be at Green Gables.
She provides Anne and her friends with light bulbs from her home after their purchased bulbs were broken.
She provides sanctuary to Cole Mackenzie after he decided not to stay at Avonlea.
- Series creator Moira Walley-Beckett spoke to IndieWire about layering the character of Aunt Josephine:
“Upon reading [the novel] again as an adult, I was wondering about Aunt Jo,” said Walley-Beckett. “In the book, she’s a spinster and she’s just a bit of a curmudgeon, and that’s kind of it. So I’m like, ‘Well, she coming to the Barrys for a month and she’s grieving,’ that’s why I decided to justify why she’s there: Who is she grieving?”
- That answer came in Season One, when the wealthy Aunt Jo revealed that she was mourning the loss of the person whom young Diana Barry thought of as Aunt Gertrude, Josephine’s partner. Although the term didn’t exist at the time, their relationship was a “Boston marriage,” the cohabitation of two women independent of financial support from a man. While the Barrys merely saw this as a friendship, Josephine and Gertrude were in truth a lesbian couple.
“It seemed like a perfect opportunity for me to dive into the reality of a Boston marriage that was secret, as it would have been at that time,” said Walley-Beckett. “And so we touch on that in Season 1, and in Season 2 we get to expand upon it in a way that allows her to provide a forum of acceptance and safe haven for Cole and the other people in her community.” 
- Her partner, Gertrude, would always spoil the ending of whatever book she was reading, so Josephine had to hide them from her.